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Triethyl phosphite
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<h2 id="reactions">Reactions</h2> <p>Triethyl phosphite can react with electrophiles in a <a href="/facts/Michaelis%E2%80%93Arbuzov_reaction/onSeyEBT">Michaelis–Arbuzov reaction</a> to produce organophosphonates. For example, the reaction between triethyl phosphite and <a href="/facts/Ethyl_bromoacetate/PEBHk6b6">ethyl bromoacetate</a> produces a phosphonate suitable for use in the <a href="/facts/Horner%E2%80%93Wadsworth%E2%80%93Emmons_reaction/w3xVWSrw">Horner–Wadsworth–Emmons reaction</a>.<a class="footnote-ref" id="fnref:2" href="#fn:2"><sup>2</sup></a> </p> <p>Reduction/deoxygenation of <a href="/facts/Hydroperoxide/w7hdgtVF">hydroperoxides</a> to the alcohols can also be effected using triethyl phosphite.<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a> This approach can be utilized for carbonyl α-hydroxylation by reacting the enolate with oxygen, producing an α-hydroperoxide which can be reduced by triethyl phosphite to the alcohol.<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a> A proposed mechanism is shown below.<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a> </p> <p>Triethyl phosphite can also be used in the <a href="/facts/Corey%E2%80%93Winter_olefin_synthesis/FnFL2aeb">Corey–Winter olefin synthesis</a>.<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a> </p> <h3>As a ligand</h3> <p>In <a href="/facts/Coordination_chemistry/1tCyeQUm">coordination chemistry</a> and <a href="/facts/Homogeneous_catalysis/c7wplnb2">homogeneous catalysis</a>, triethylphosphite finds use as a <a href="/facts/HSAB/yguwscxc">soft</a> ligand. Its complexes are generally lipophilic and feature metals in low oxidation states. Examples include the colorless complexes FeH2(P(OEt)3)4 and Ni(P(OEt)3)4 (m.p. 108 °C).<a class="footnote-ref" id="fnref:7" href="#fn:7"><sup>7</sup></a> It also forms a stable complex with <a href="/facts/Copper(I)_iodide/M46Pz9yo">copper(I) iodide</a>.<a class="footnote-ref" id="fnref:8" href="#fn:8"><sup>8</sup></a> </p> <h2 id="external-links">External links</h2> <ul><li><a href="https://www.eastman.com/Literature_Center/G/GN330.pdf">Eastman triethyl phosphate (TEP)</a></li> <li><a href="http://webbook.nist.gov/cgi/cbook.cgi?ID=C122521">WebBook page for C6H15PO3</a></li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Ford-Moore, A. H.; Perry, B. J. (1951). "Triethyl Phosphite". Org. Synth. 31: 111. doi:10.15227/orgsyn.031.0111. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Piscopio, Anthony D.; Shakya, Sagar (2005). "Triethyl Phosphite". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt224.pub2. ISBN 0-471-93623-5. <a href="0-471-93623-5" target="_blank">0-471-93623-5</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Piscopio, Anthony D.; Shakya, Sagar (2005). "Triethyl Phosphite". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt224.pub2. ISBN 0-471-93623-5. <a href="0-471-93623-5" target="_blank">0-471-93623-5</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Gardner, J. N.; Carlon, F. E.; Gnoj, O. (1968). "One-step procedure for the preparation of tertiary α-ketols from the corresponding ketones". The Journal of Organic Chemistry. 33 (8): 3294–3297. doi:10.1021/jo01272a055. PMID 5742870. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Liang, Yu-Feng; Jiao, Ning (2014). "Highly Efficient C–H Hydroxylation of Carbonyl Compounds with Oxygen under Mild Conditions". Angewandte Chemie International Edition. 53 (2): 548–552. doi:10.1002/anie.201308698. PMID 24281892. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>Piscopio, Anthony D.; Shakya, Sagar (2005). "Triethyl Phosphite". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt224.pub2. ISBN 0-471-93623-5. <a href="0-471-93623-5" target="_blank">0-471-93623-5</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><p>Ittel, Steven D. (1990). "Complexes of Nickel(0)". Inorganic Syntheses. Inorganic Syntheses. Vol. 28. pp. 98–104. doi:10.1002/9780470132593.ch26. ISBN 978-0-470-13259-3. <a href="978-0-470-13259-3" target="_blank">978-0-470-13259-3</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li> <li id="fn:8"><p>Piscopio, Anthony D.; Shakya, Sagar (2005). "Triethyl Phosphite". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt224.pub2. ISBN 0-471-93623-5. <a href="0-471-93623-5" target="_blank">0-471-93623-5</a> <a href="#fnref:8" class="footnote-back-ref">↩</a></p></li> </ol>